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Paul Pagliaro started their work experience in 1997 as the Vice President and Head of CIBC Trust and Wealth Management at CIBC Wealth Management. Paul later became the Director of Marketing for Global Private Banking at the same company. In 2002, they became the President and CEO of Milano Software. From 2014 to 2015, Pagliaro served as the Senior Vice President of Products at HRSG. Paul then worked as a Principal at a Business and Management Consulting firm from 2001 to 2016. During this time, they built a division of a financial institution, grew a software company, and developed an exit plan for small to mid-sized companies. In 2016, they joined Jonas Software as the Director of Business Development, Mergers, and Acquisitions. In 2019, Pagliaro became the CEO of GuestVision, a subsidiary of Jonas Software. Currently, starting in 2022, they are serving as the Vice President of Strategic Initiatives for Jonas Software Australia, overseeing US operations.

Paul Pagliaro attended Lockview Secondary School, but no further information about their education history is available.